"Dear Summer" is the third and final single from Memphis Bleek's fourth album, 534. The single is somewhat unusual because the song features no vocals from Memphis Bleek, the host of the song. The song only features vocals from featured guest, Jay-Z. At the time, Jay-Z was a retired rapper just making an appearance on his label-mate's song. The beat dropped and Jay began freestyling and they recorded the song when it was done without Bleek having rapped. He made the choice to give it to Jay-Z but still place it on his album and release it as a single. It was produced by Just Blaze. It contains a sample from Weldon Irvine's "Morning Sunrise". Jay-Z released his first song since beginning his brief "retirement". The song was called "Dear Summer", in reference to what Jay called the time of the year when he would drop a classic album or single every year for 8 straight years, and how he had to metaphorically leave "her", Summer."Jigga has some great rhymes about his decision to leave performance for his job as Def Jam's CEO".
A line from the song later became interpreted as a diss at The Game for making songs subliminally dissing Jay-Z. "It's like when n**** make subliminal records/If it ain't directed directly at me, I don't respect it/You don't really want it with Hov, for the record/I put a couple careers on hold, you could be next, kid/Keep entering the danger zone/You gon' make that boy Hov put your name in a song".